5-溴-3-氯吲唑 → 2,2'-二吡咯基甲烷

HRID 2425463笔记

反应方程式

HRID 2425463 反应方程式
[CH:1]1[CH:5]=[C:4]([CH2:6][C:7]2[NH:11][C:10](C=O)=[CH:9][CH:8]=2)[NH:3][CH:2]=1.C12C=C3N=C(C=C3)C=C3NC(C=C3)=CC3=NC(C=C3)=CC(N1)=CC=2>>[CH:9]1[CH:8]=[C:7]([CH2:6][C:4]2[NH:3][CH:2]=[CH:1][CH:5]=2)[NH:11][CH:10]=1

参与物

3

反应物 2

HCID 167326915-溴-3-氯吲唑HCID 137705241卟吩

产物 1

HCID 1408142,2'-二吡咯基甲烷收率 46%

实验过程

1-Formyldipyrromethane 2 is the key precursor for the porphine synthesis described herein. Formylation of dipyrromethane via Vilsmeier or Grignard reagent mediated syntheses21 results in multiple byproducts, requiring tedious chromatographic separation for the purification of 1-formyldipyrromethane (2). The TLC and 1H NMR analyses of the crude reaction mixture obtained from Vilsmeier formylation of dipyrromethane showed the presence of three components: starting dipyrromethane (3), 1-formyldipyrromethane (2), 1,9-diformyldipyrromethane (4), and an unknown byproduct (tentatively assigned as a 2-formyldipyrromethane) in a ratio of 7:20:4:1. We were able to separate the desired 2 in 46% yield (without using a tin complexation strategy); however, the purification required lengthy column chromatography.

来源与证据

ORD记录
ord-e34635bbb85a4147a9970b8885fea68d
来源数据集
uspto-grants-2011_06
专利号
US07964720B2

反应笔记

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